Carbenoxolone

Carbenoxolone Basic information
Product Name:Carbenoxolone
Synonyms:CARBENOXOLONE;3β-[(β-Carboxypropionyl)oxy]-11-oxoolean-12-en-30-oic acid;glycyrrhetinic acid hydrogen succinate;3beta-Hydroxy-11-oxoolean-12-en-30-oic acid hydrogen succinate;Olean-12-en-29-oic acid,3-(3-carboxy-1-oxopropoxy)-11-oxo-,(3b,20b)-;CARBENOXOLONE(RG);2-Methylidene-2,3-dihydrofuran-3-one;CARBENOXOLONE [U
CAS:5697-56-3
MF:C34H50O7
MW:570.76
EINECS:227-174-2
Product Categories:Pentacyclic Triterpenes
Mol File:5697-56-3.mol
Carbenoxolone Structure
Carbenoxolone Chemical Properties
Melting point 291-294 °C
alpha D20 +128° (chloroform)
Boiling point 553.75°C (rough estimate)
density 1.20
refractive index 1.5820 (estimate)
storage temp. -20°C Freezer
solubility Chloroform (Slightly), Methanol (Slightly)
pkapKa 6.7 (Uncertain)
form Solid
color Cream crystals
Water Solubility 6.621mg/L(24 ºC)
CAS DataBase Reference5697-56-3(CAS DataBase Reference)
EPA Substance Registry SystemOlean-12-en-29-oic acid, 3-(3-carboxy-1-oxopropoxy)-11-oxo-, (3.beta.,20.beta.)- (5697-56-3)
Safety Information
ToxicityLD50 orl-rat: 2450 mg/kg OYYAA2 19,323,80
MSDS Information
Carbenoxolone Usage And Synthesis
OriginatorBiogastrone,Winthrop,UK,1963
UsesGlucocorticoid.
Manufacturing Process23.5 g of glycyrrhetinic acid were dissolved in 50 cc of dry pyridine. A solution of 6.0 g of succinic anhydride in 30 cc of dry pyridine was added, followed by 30 cc of dry triethylamine and then, for washing purposes, 5 cc of dry pyridine. The solution was heated on a boiling water bath for ten hours and then poured into excess of dilute hydrochloric acid and ice. The fine gray precipitate formed was filtered off, washed with water, dissolved in chloroform, and the solution repeatedly extracted with dilute hydrochloric acid and later with water. It was dried over sodium sulfate and evaporated to dryness. Crystallization from methanol, using charcoal to effect decolorization, gave the hydrogen succinate as cream-colored crystals, MP 291° to 294°C, with previous softening.
One molecular proportion of glycyrrhetinic acid hydrogen succinate was ground with a dilute (5%) aqueous solution containing two molecular proportions of sodium hydroxide. The solution was filtered and evaporated in vacuum over concentrated sulfuric acid. The sodium salt is then obtained as a creamy white water-soluble solid. Glycyrrhetinic acid is obtainable from licorice root.
Therapeutic FunctionAntiinflammatory (gastric)
Safety ProfilePoison by intravenous andintraperitoneal routes. Moderately toxic by ingestion andsubcutaneous routes. Human systemic effects byingestion: muscle weakness and flaccid paralysis. Whenheated to decomposition it emits acrid smoke and fumes.
Carbenoxolone Preparation Products And Raw materials
Raw materials18β-Glycyrrhetinic Acid-->Succinic anhydride
ColloidalBismuthPectin Sucralfate Hydrogen Sulfide CARBENOXOLONE, DICHOLINE SALT CARBENOXOLONE DISODIUM SALT,CARBENOXOLONE SODIUM,carbenoxolone disodium,Carbenoxolone sodium [USAN:JAN] Hydrogen peroxide Cicloxolone CARBENOXOLON SODIUM 6alpha-Methylprednisolone sodium succinate DGL 18alpha-carbenoxolone HYDROGEN SELENIDE HYDROGEN CYANIDE Hydrogen 18β-Glycyrrhetinic Acid GADOLEICACID CHLOROPHOSPHONAZO III Carbenoxolone

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